What To Wear To Go Apple Picking: 5 Fool-Proof Tips

Last weekend, I had the pleasure of traveling from my measly suburban Central New Jersey town to the picturesque rolling hills of upstate Gardnertown, New York to spend some quality time apple picking with my family. I hadn’t been for almost a decade, so I was inordinately excited to get my hands on some fresh apple cider and cinnamon donuts. I figured I’d enjoy the scenery and leave the hard work (i.e. actual apple picking) to my uncles, who could lift up my young cousins to take their pick, so I wore my favorite beat up flats, a pair of boyfriend jeans and a sweater. I was seriously ill-prepared.

Now that I’m one apple picking trip wiser, take it from me: here are five essential tips for spending the day roaming through an orchard in October, straight from our new book, Wear This Now.

1. Wear sneakers or boots with thick socks. You’ll be doing tons of walking (it’s amazing how many types of apple trees there are), and you’ll regret wearing footwear without any support. If you’re wearing anything open-toed, a few rotten apples will probably land on your feet because, you know, Murphy’s Law.

2. Resist the urge to throw on a pair of leggings or sweats (or worse, a dress!) that could rip if you’re battling branches. Instead, opt for a pair of skinny cargo jeans with tons of pockets for storing the goods.

3. Bring sunglasses. It may be October, but you’ll spend a lot of the day looking up into the trees, right where the sun is hovering. Protect your eyes and look chic in a pair of oversized Karen Walker sunnies or Persol Aviators.

4. Now’s the time to break out that down vest that’s been hiding at the back of your closet since last fall. Layer it over a comfy sweater that allows for all the inevitable reaching. Store an oversized parka in the car just in case it gets chilly.

5. Bring a hat. Unless you’re up at the crack of dawn, the sun will probably start setting before you’re ready to check out. You’ll need the extra coverage then.

For more tips and tricks on how to dress for any occasion, pick up our new book, Wear This Now, or check out the 5 fashion commandments to live by, what to wear to fashion week, or read up on the best styling tricks for when you’re sick of your closet.